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Amberlite IRA-400 Cl Resin Catalyzed Multicomponent Organic Synthesis in Water: Synthesis, Antimicrobial and Docking Studies of Spiroheterocyclic 2-Oxindoles and Acenaphthoquinone

[ Vol. 5 , Issue. 1 ]

Author(s):

Gurusamy Harichandran*, Krishnan Sarojini Devi, Ponnusamy Shanmugam, Michael Immanuel Jesse and Krishnan Kathiravan   Pages 13 - 24 ( 12 )

Abstract:


Background: To investigate the multicomponent organic synthesis of the biologically important spiro-oxindoles, spiro-acenaphthoquinone and spirochromenes scaffolds by using Amberlite IRA-400 Cl resin as catalyst in an aqueous medium.

Methods: Three-component synthesis of spiro components has been achieved by the reaction of isatin/ acenaphthoquinone/ninhydrin, activated methylenes, and 1,3-dicarbonyl compounds under catalytic amount of Amberlite IRA-400 Cl resin in an aqueous medium. This protocol is significant due to its environmentally benign nature, efficiency, and easy handling.

Results: A large number of spiro heterocyclic compounds have been synthesized by using efficient and environmentally benign Amberlite IRA-400 Cl resin catalyst. The synthesized compounds have displayed considerable antimicrobial activities against human pathogenic bacteria and fungi. The in silico studies revealed that these compounds are good antimicrobial agents as it showed lower binding energy and higher binding affinity towards the active binding pocket in the receptors transglycosylase of bacteria and glucoamylase of fungi.

Conclusion: A number of spirochromene, spiroacenaphthylene and spiro-oxindoles derivatives have been synthesized using Amberlite IRA-400 Cl resin as catalyst in water medium. Selective synthesized compounds 4h, 4j, 6d and 6g have been proved to be antimicrobial agent against the entire test pathogens compared to commercial agents. Molecular docking studies revealed that even at a low concentration with exhibit lower binding energies and higher binding affinity in order to maintain the stable protein-ligand binding complex with the enzymes transglycosylase of bacteria and glucoamylase of fungi proves the compounds are possess strong antimicrobial property.

Keywords:

Amberlite resin, antibacterial activities, aqueous medium, docking, multicomponent reaction, spiroheterocyclic oxindole.

Affiliation:

Department of Polymer Science, University of Madras, Guindy Campus, Chennai, Department of Polymer Science, University of Madras, Guindy Campus, Chennai, Organic and Bioorganic Chemistry Division, CSIR-Central Leather Research Institute, Adyar, Chennai-20, Department of Biotechnology, University of Madras, Guindy Campus, Chennai, Department of Biotechnology, University of Madras, Guindy Campus, Chennai

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